An unprecedented electronic preference for the "meta" product in Diels-Alder reactions of ethynyldialkylboranes. [(Trimethylsilyl)ethynyl]-9-BBN as a reactive and versatile dienophile
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[(Trimethylsilyl)ethynyl]-9-BBN undergoes Diels–Alder reactions with acyclic dienes at 100 °C to afford 1,4-cyclohexadienes in high yields. The novel regiochemistry of these reactions is consistent with an ab initio prediction of advanced bonding to boron in a [4 atom + 3 atom] transition state. © 1992, American Chemical Society. All rights reserved.
author list (cited authors)
Singleton, D. A., & Leung, S. W.